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You know, almost every single answer is 'hiking." The city-zens here are born loving, or move here loving, or soon learn to love, the outdoors. And as far as the questions go:
2. Hiking at Split Rock, on the Superior Hiking Trail -- close to Duluth -- then dinner at Scenic Cafe.
3. Hiking the doable-but-grueling 15-mile trail on Angleworm Lake, up by the Boundary Waters -- dining provided by Camelbaks and Clif Bars. You can't be a baby and still hike this.
4. Hiking at Cascade River -- the most beautiful trail on the SHT -- dinner at Chez Jude afterward.
5. Any SHT overlook onto Lake Superior.
As for the first question -- I'm old, I've forgotten how to date, better ask the youngsters.

(1) If Duluth were after an eligible date prospect, where would Duluth look? A rally, a public meeting.
(2) If Duluth were taking somebody out on a first date and needed to impress them, what would Duluth pick? Scenic Cafe,for a show of food taste and the view on the way back.
(3) If Duluth were on an early relationship date and really wanted to test the date's mettle, what would Duluth pick? Bar crawl in Superior with the full Chester hike/ski the next morning.
(4) If Duluth were settled into a longterm relationship, what would their regular date spot be? Zinema.
(5) If Duluth were going to propose, what spot would Duluth pick to do it? Enger Tower, for Freudian purposes and the view.

(3) A beach day at Lake Superior. Want to know how much chutzpah someone has? Ask them to go for a swim in the lake!
(4) UMD Hockey Games. A burger at The Anchor.
(5) On the beach, where you asked them to go for a swim. You knew they were the one when they got into that freezing water and didn't complain.